A few weeks ago we wrote our reflections on 2000 days as digital nomads, looking back at the highs and lows of life on the road, living out of a backpack and working online. In today’s post we answer your questions about our lifestyle.
How do you afford to travel?
We’re digital nomads which means we work online so we can work from anywhere as long as we have access to the internet.
When we first started Simon did freelance web design but after a few years he taught himself to make iOS apps and created Trail Wallet, an easy travel expense tracker. He no longer does client work and instead focuses on his own projects. I work on this travel blog which earns an income from advertising, sponsorships, and affiliate commissions. I’ve also done a few freelance writing assignments.Read more about how we fund our travels.
What’s your favourite country?
We don’t have one favourite country and this question gets more difficult to answer the more we travel.
We love Italy for its food and beauty; Japan for its quirkiness, efficiency, and wonderfully polite people; and India for its nonstop craziness, vibrant life, and vegetarian friendliness.
We often return to Thailand (especially Chiang Mai and Koh Lanta) as it’s a great digital nomad destination (low cost of living, apartments to rent, good WiFi) with delicious food, beautiful temples, mountains and beaches, and friendly people.
There are countries we’ve really enjoyed travelling to and highly recommend to others like Slovenia, Jordan, and Cuba, but that we haven’t spent much time in so its hard to call them favourites.
We love to visit the US—especially Portland, San Francisco (and all of California), and Disney World.
It really is impossible to choose a favourite as everywhere has something different to offer.

Piazza Navona in Rome. Italy pulls us back again and again.
How do you choose where to go next?
Many factors: weather (we follow the sun), the need for change (we tend to divide each year between Europe and Asia or Latin America), a craving for certain foods, weddings and other family events, the availability of apartment rentals/WiFi/vegetarian food.
We usually only fly long haul twice a year so we stay a while on continents and visit countries that are close by. We have a long wish list of places to visit so we see where is pulling us most strongly.
Do you get tired of moving around? How do you balance work and travel?
We definitely get tired of moving around sometimes so we tend to travel slowly spending at least a week or sometimes a month in one place, with a couple of 2-3 month stints in one place each year. Slow travel is essential for balancing work and travel—if we stay somewhere for longer periods of time we have time for work and exploration, and can get into routines that help our productivity.
I’ve written more about this issue in our reflections on 2000 days as digital nomads.
How do you manage your relationship as a couple and as business partners? How do you decide who does which tasks? Do you ever need time apart?
We’ve been together for 16 years (since we were 18) and have always been a very close couple who spend a lot of time together. Long term travel is probably the ultimate test for relationships as you are together 24/7, often in stressful situations (Till the Money Runs Out have a great article on why couples should travel before marriage), but we’ve found we thrive on it and get on even better than we did before we travelled, probably because we’re happier.
We don’t feel the need to spend time apart but we do naturally do some things separately—in the last few years I’ve started running and yoga which I can’t quite convince Simon to join me in, and when we’re working we’re usually in separate areas, even if it’s in the same room.
Our roles have emerged naturally based on our skills and interests—Simon does anything technical or design related (including creating Trail Wallet, designing the blog, and general computer/website maintenance); I do most of the writing and photography on the blog, and all the travel planning; I cook, Simon washes up.
We used to argue about business decisions but I think that came from fear and from feeling we should do things that we really didn’t want to do. Since we accepted that we’re not motivated by money and only want to work on things we enjoy (read more about how we found our own path) it hasn’t been a problem.

Us in the jacuzzi of our villa on Koh Lanta
Do you get lonely? Do you meet other expats on the road?
We don’t get lonely because we have each other. Through our blog we’ve made lots of friends with other nomads and often cross paths with them around the world, especially in digital nomad hotspots like Chiang Mai. When we stay in one place for a few months we sometimes get to know expats who are living there, but we’re more likely to meet up with other nomads and bloggers.
If you are a solo traveller you are likely to meet a lot more people than we do as we tend to be pretty self contained. There are always opportunities to meet people including staying in hostels, co-working spaces, Facebook groups, and couchsurfing meetups.
Do you miss home and how often do you go back?
After over five years away we don’t consider England home anymore and have no desire to live there again. We go back about once a year in the summer (which is the coldest weather we experience all year!) to see friends and family and take care of practical things like visits to our doctor and dentist. We usually coincide our visits with events like weddings and major birthdays. We haven’t spent Christmas with family since we left, and it is something we’re considering as we do miss family at that time (and it never feels Christmassy in the tropics!), but England in December isn’t very appealing!
We find that although we see our family less often than before we spend longer periods of time with them, and we’ve also enjoyed people coming out and visiting us.
If you are considering nomadic life but are worried about missing home then remember that you get to set the rules—you can go back as often and for as long as you like. That’s the beauty and freedom of this lifestyle.

Simon and his mum, who recently visited us in Bali
Do you plan to have kids and would you travel with them?
We aren’t going to have kids but plenty of families travel long term together—here’s a list of 14 of them and there are many more.
How do you track your expenses and manage your finances abroad?
Ever since we starting saving for travel we’ve kept track of every penny we’ve spent—first using spreadsheets and for the last three years using Trail Wallet, an iOS app that Simon created to help us and other travellers stay on budget. It makes tracking your expenses really easy and does all the currency conversions for you.

Our Trail Wallet app
We manage our bank accounts using online banking, and withdraw cash from ATMs when we arrive in new countries. We carry multiple credit and debit cards in case anything goes wrong with one, and we always have an emergency supply of US dollars. You can read more about how we manage our finances.
Do you think it’s a good idea to consider becoming a digital nomad before you actually have sufficient clients?
In an ideal world you’d have an established business before you left but we didn’t (Simon had one freelance project from his previous employer). We saved up enough to keep us going for about a year in South America while we grew our business (we didn’t end up needing most of the savings but it’s good to have as our income varies), and we’d definitely recommend having savings.
Set yourself a deadline to leave and in that time save up and try to gain clients or grow your business, but then go anyway. There’s never a right time, and in many parts of the world you can live inexpensively while you work on your business.
What do you do about healthcare and travel insurance?
We use True Traveller for travel insurance as they are one of the few insurance companies that lets you purchase a new policy when you are already abroad and without a ticket home. They are a great option if you are from the UK or EU, and for everyone else we recommend World Nomads who we’ve used in the past—they are more expensive but very reliable and used by many digital nomads. We’ve written a more detailed post about travel insurance.
We have typhoid, diptheria, tetanus, Hepatitis A, and Hepatitis B vaccinations which we get boosters of when needed in the UK or in places like Chiang Mai where we have a doctor we trust. We also got yellow fever before we visited South America. We don’t take malaria medication as most places we visit are low risk—we use the Fit for Travel NHS website to decide.
We’ve been lucky not to be seriously ill on our travels and have only been to doctors in Thailand for minor issues and for rabies vaccinations (after Simon was scratched by a monkey and I had a minor bite from a dog, on separate incidents!). We found the healthcare good and prices low.
Of course, we are not doctors so you should always seek proper medical advice before travelling.
How do you manage to refrain from collecting souvenirs along the way? With carry-on luggage only you wouldn’t have space for memorabilia or precious possessions.
We don’t buy souvenirs at all. In the process of saving for travel we lost our interest in shopping so we’re never tempted. Our memories and photos of our experiences are more important to us than any physical souvenir.
If you do love to shop but are travelling light then you could focus on small and wearable things like jewellery, scarves, and clothes. You could also post items home.
How on earth do you travel with just a carry-on backpack?

Us with our carry-on backpacks
By prioritising. We only travel with things we use regularly—everything has to earn its place and we never pack things “just in case”. We bought carry-on sized backpacks (Simon has the Tortuga, I have the Osprey Farpoint 40) so we had no choice but to only pack what could fit inside, and we use packing cubes to maximise space. We can mix and match all our clothes, a kindle saves on book weight, and we’ve minimised our toiletries.
It might seem difficult at first but you really do get used to it—even if we had more clothes I’m sure we’d just wear the same things. Travelling light makes life so much easier that we can’t imagine travelling with more.
I’m currently writing a book about how to travel carry-on only, whether you are travelling for a week or a year (sign up to our newsletter to stay updated), but in the meantime you can see our packing list, our tips on travelling with just a carry on, and our review of our carry-on backpacks.
Do you have any regrets? And if you could have done anything differently, what would it be?
Simon wishes he had started making apps sooner as we had the idea for Trail Wallet two years before he actually built it. We would be much further along if we had created it then. Still, of all the regrets to have, it’s a minor one and the lesson was follow your muse first and worry about money second.
Our only travel regret is not going to the Galapagos Islands while we were in South America. We were worried about the cost but it would have been fine. There’s a theme emerging here…
Do you plan to settle down? If you had to choose a place to live where would it be?
We can’t imagine settling down as we love the freedom of this lifestyle too much. There are plenty of places we’d be happy to return to regularly—Chiang Mai and Koh Lanta in Thailand, Ubud in Bali, San Francisco and Portland in the US, and anywhere in Italy—but we wouldn’t want to live in any of them year round. We like to mix up city, country and beach life; tropical winters and European summers; and choosing just one place to live feels too restrictive.
You can also read our posts about the practicalities of life as digital nomads. Part 1 covers health, banking, and retirement, and Part 2 discusses tax, visas, internet, phones, one way flights, and security.
Thanks to everyone who submitted questions on Facebook and by email!
Do you have any other questions about our nomadic lifestyle? Leave a comment and let us know.